2,14-Dioxapentacyclo[20.2.2.210,13.13,7.115,19]triaconta-3,5,7(30),10,12,15,17,19(27),22,24(1),25,28-dodecaene-4,12-diol

Base Information

• Chemical Name: 2,14-Dioxapentacyclo[20.2.2.210,13.13,7.115,19]triaconta-3,5,7(30),10,12,15,17,19(27),22,24(1),25,28-dodecaene-4,12-diol
• CAS No.: 85318-27-0
• Molecular Formula: C₂₈H₂₄O₄
• Molecular Weight: 424.496
• Mol file: 85318-27-0.mol

Synonyms:

Chemical Property of 2,14-Dioxapentacyclo[20.2.2.210,13.13,7.115,19]triaconta-3,5,7(30),10,12,15,17,19(27),22,24(1),25,28-dodecaene-4,12-diol

Chemical Property:

• PSA: 58.92000
• LogP: 6.56620

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,14-Dioxapentacyclo[20.2.2.210,13.13,7.115,19]triaconta-3,5,7(30),10,12,15,17,19(27),22,24(1),25,28-dodecaene-4,12-diol

There total 31 articles about 2,14-Dioxapentacyclo[20.2.2.210,13.13,7.115,19]triaconta-3,5,7(30),10,12,15,17,19(27),22,24(1),25,28-dodecaene-4,12-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

riccardin B di-O-methyl ether (85318-29-2) → riccardin B (85318-27-0)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(00)94949-9

Reference yield:

4-methoxycarbonylphenyl bromide (619-42-1) → riccardin B (85318-27-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 79 percent / K₂CO₃-CuO / pyridine / Heating

2: p-TsOH

3: LiAlH₄

4: SOBr₂

6: p-TsOH

7: 84 percent / t-BuOk / dimethylformamide

8: H₂ / PtO₂

9: LiAlH₄

10: SOBr₂

12: 89 percent / t-BuOK / dimethylformamide

13: H₂ / PtO₂

14: BBr₃

With lithium aluminium tetrahydride; sulfurous dibromide; potassium tert-butylate; hydrogen; boron tribromide; potassium carbonate; copper(II) oxide; platinum(IV) oxide; toluene-4-sulfonic acid; In pyridine; N,N-dimethyl-formamide;

DOI:10.1246/cl.1985.1587

Reference yield:

methyl 4-(5'-formyl-2'-methoxyphenoxy)benzoate (101110-74-1) → riccardin B (85318-27-0)

Guidance literature:

Multi-step reaction with 13 steps

1: p-TsOH

2: LiAlH₄

3: SOBr₂

5: p-TsOH

6: 84 percent / t-BuOk / dimethylformamide

7: H₂ / PtO₂

8: LiAlH₄

9: SOBr₂

11: 89 percent / t-BuOK / dimethylformamide

12: H₂ / PtO₂

13: BBr₃

With lithium aluminium tetrahydride; dibromo sulfoxide; potassium tert-butylate; hydrogen; boron tribromide; platinum(IV) oxide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1246/cl.1985.1587

upstream raw materials:

riccardin B di-O-methyl ether

isovanillin

4-hydroxy-3-methoxybenzoic acid methyl ester

m-bromobenzoic aldehyde

Refernces

• 1、 Iyoda,Sakaitani,Otsuka,Oda. "Synthesis of riccardin B by nickel-catalyzed intramolecular cyclization". . p. 4777 - 4780. Retrieved 2007/10/02.